Skip to main content
Log in

Synthesis and electrochemical studies of new styrenic poly(ionic liquid)s based on the 1-methyl-1,2,3-benzotriazolium cation

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The styrenic ionic liquid-based poly ionic liquids (PILs) with the advantage of facile synthesis and the ability to incorporate many desirable functional moieties offer an efficient route to highly functional styrenic PILs. On the other hand, triazole is a desirable and useful heterocyclic compound that can be used in various fields of polymer and material science to attain better properties. In this paper, a set of new styrenic ionic liquid monomers based on 1-methyl-1,2,3-benzotriazolium cation were successfully synthesized by a quaternization of 1-methyl-1,2,3-benzotriazole with 4-vinylbenzylchroride. Subsequently, an anion exchange reaction was carried out. Afterward, these styrenic ionic liquid monomers readily polymerized via free radical polymerization. The chemical structures of these monomers and polymers were confirmed by Fourier transform infrared spectroscopy and proton and carbon nuclear magnetic resonance (1H- and 13C-NMR). Furthermore, the solubility of the homopolymers in different solvents was tested. The thermal behavior of the polymers was evaluated by thermogravimetric analysis and differential scanning calorimetry. The cyclic voltammetery measurements revealed that these polymers have a larger electrochemical window compared with polystyrene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. T. Erdmenger, C. Guerrero-Sanchez, J. Vitz, R. Hoogenboom, U.S. Schubert, Chem. Soc. Rev. 39, 3317 (2010)

    Article  CAS  Google Scholar 

  2. J. Lu, F. Yan, J. Texter, Prog. Polym. Sci. 34, 431 (2009)

    Article  CAS  Google Scholar 

  3. M. Xiao, Free Radical Polymerization in Room Temperature Ionic Liquids. Master’s thesis, University of Tennessee, (2006)

  4. H. Zhang, K. Hong, J.W. Mays, Macromolecules 35, 5738 (2002)

    Article  CAS  Google Scholar 

  5. J. Yuan, D. Mecerreyes, M. Antonietti, Prog. Polym. Sci. 38, 1009 (2013)

    Article  CAS  Google Scholar 

  6. Y. Men, D. Kuzmicz, J. Yuan, Curr. Opin. Colloid Interface Sci. 19, 76 (2014)

    Article  CAS  Google Scholar 

  7. J. Yuan, M. Antonietti, Polymer 52, 1469 (2011)

    Article  CAS  Google Scholar 

  8. P. Dimitrov-Raytchev, S. Beghdadi, A. Serghei, E. Drockenmuller, J. Polym. Sci., Part A: Polym. Chem. 51, 34 (2013)

    Article  CAS  Google Scholar 

  9. J. Mythri, B.S. Anusha, M. Srinivasa Reddy, J. Chem. Pharm. Sci (2014) ISSN: 0974-2115

  10. R. Sood, M.M. Obadia, B.P. Mudraboyina, B. Zhang, A. Serghei, J. Bernard, E. Drockenmuller, Polym. 55, 3314 (2014)

    Article  CAS  Google Scholar 

  11. P. Wang, Y.-N. Zhou, J.-S. Luo, Z.-H. Luo, Polym. Chem. 5, 882 (2014)

    Article  CAS  Google Scholar 

  12. B.J. Adzima, S.C. Taylor, H. He, D.R. Luebke, K. Matyjaszewski, H.B. Nulwala, J. Polym. Sci., Part A: Polym. Chem. 52, 417 (2014)

    Article  CAS  Google Scholar 

  13. J. Yang, J. Zheng, J. Zhang, L. Sun, F. Chen, P. Fan, M. Zhong, RSC Adv. 5, 32853 (2015)

    Article  CAS  Google Scholar 

  14. E.B. Anderson, T.E. Long, Polymer 51, 2447 (2012)

    Article  Google Scholar 

  15. C. Detrembleur, A. Debuigne, M. Hurtgen, C. Jerome, Macromolecules 44, 6397 (2011)

    Article  CAS  Google Scholar 

  16. D. Mecerreyes, Prog. Polym. Sci. 36, 1629 (2011)

    Article  CAS  Google Scholar 

  17. S. Koguchi, K. Izawa, ACS combinatorial science. 16, 381 (2014)

    Article  CAS  Google Scholar 

  18. S.A. Forsyth, D.R. MacFarlane, J. Mater. Chem. 13, 2451 (2003)

    Article  CAS  Google Scholar 

  19. A. Mudzakir, Indonesian J. Chem. 6, 111 (2006)

    Google Scholar 

  20. N.H. Buttrus, A.A. Sabah, A.A. Taqa, U. Englert, Acta Cryst. 68, 02735 (2012)

    Google Scholar 

  21. S. Sanghi, E. Willett, C. Versek, M. Tuominen, E.B. Coughlin, RSC Adv. 2, 848 (2012)

    Article  CAS  Google Scholar 

  22. W. Zhang, J. Yuan, Macromol. Rapid Commuin. 37, 1124 (2016)

    Article  CAS  Google Scholar 

  23. B.P. Mudraboyina, M.M. Obadia, I. Allaoua, R. Sood, A. Serghei, E. Drockenmuller, Chem. Mater. 26, 1720 (2014)

    Article  CAS  Google Scholar 

  24. S. Zhang, Y. Hou, W. Huang, Y. Shan, Electrochim. Acta 50, 4097 (2005)

    Article  CAS  Google Scholar 

  25. W. Yuan, H. Jin, J.-K. Chung, J. Zheng, Chem. Biol. Interact. 186, 323 (2010)

    Article  CAS  Google Scholar 

  26. B.A. Howell, K. Chaiwong, J. Therm. Anal. Calorim. 96, 219 (2009)

    Article  CAS  Google Scholar 

  27. M. Assadi, F. Hosseinzadeh, Des. Monomers Polym. 13, 181 (2010)

    Article  CAS  Google Scholar 

  28. J.E. Bara, E.S. Hatakeyama, D.L. Gin, R.D. Noble, Polym. Adv. Technol. 19, 1415 (2008)

    Article  CAS  Google Scholar 

  29. J. Tang, H. Tang, W. Sun, M. Radosz, Y. Shen, Polym. 46, 12460 (2005)

    Article  CAS  Google Scholar 

  30. H. Tang, J. Tang, S. Ding, M. Radosz, Y. Shen, J. Polym. Sci. Part A: Polm. Chem. 43, 1432 (2005)

    Article  CAS  Google Scholar 

  31. J. Steinkoenig, F.R. Bloesser, B. Huber, A. Welle, V. Trouillet, S.M. Weidner, L. Barner, P.W. Roesky, J. Yuan, A.S. Goldmann, C. Barner-Kowollik, Polym. Chem. 7, 451 (2016)

    Article  CAS  Google Scholar 

  32. J. Tang, Y. Shen, M. Radosz, W. Sun, Ind. Eng. Chem. Res. 48, 9113 (2009)

    Article  CAS  Google Scholar 

  33. A.R. Katritzky, W. Kuzmierkiewicz, J.V. Greenhill, Recl. Trav. Chim. Pays-Bas 110, 369 (1991)

    Article  CAS  Google Scholar 

  34. F. Hosseinzadeh, M. Mahkam, M. Galehassadi, Des. Monomers Polym. 15, 379 (2012)

    Article  CAS  Google Scholar 

  35. M. Galehassadi, R. Herizchi, F. Ranjbar, Des. Monomers Polym. 14, 303 (2011)

    Article  CAS  Google Scholar 

  36. B.K.M. Chan, N.-H. Chang, M.R. Grimmett, Aust. J. Chem. 30, 2005 (1977)

    Article  CAS  Google Scholar 

  37. R.K. Donato, M.V. Migliorini, M.A. Benvegnú, J. Dupont, R.S. Gonçalves, H.S. Schrekker, J. Solid State Electtrochem. 11, 1481 (2007)

    Article  CAS  Google Scholar 

Download references

Acknowledgement

The authors appreciate Dr. Rahim Mohammad-Rezaei for the cyclic voltammetry studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohammad Galehassadi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 360 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jahed, F.S., Galehassadi, M. Synthesis and electrochemical studies of new styrenic poly(ionic liquid)s based on the 1-methyl-1,2,3-benzotriazolium cation. Res Chem Intermed 44, 3375–3388 (2018). https://doi.org/10.1007/s11164-018-3313-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3313-4

Keywords

Navigation